ALL CHALKBOARDS

Wednesday, September 10, 2025

September 10th, 2025

 What if tonight is the last night you go to bed?

That is what September 10th is. It is the last night thousands of people went to sleep thinking they would wake up Tuesday morning, kiss their kids, walk the dog, grab a coffee, make the opening bell and have a normal day.
But they didn’t.
They had their last day.
For me, September 10th, 2001, was softball night. I pulled on a pair of softball pants, threw on my Wild Turkey jersey, and drove over to Ridgeland Common for the first game of the fall season. Oak Park autumn ball isn’t like summer ball, the games move fast. Every batter starts with a 1-and-1 count. By the end of the season, we are playing under stadium lights at 9:30 at night with wind chills, so shaving off pitches was survival.
First at-bat, I step in, brain on autopilot, and rope one down the first-base line foul. That’s strike two. Next pitch floats in, high and lazy, clear ball… ump rings me up. I forgot about the fall pitch count and struck out without taking a last swing.
The Wild Turkeys bench exploded... not angry, but delighted. Because in our dugout, you strike out, you buy shots, and back in 2001, Irish car bombs were the weapon of choice. Twelve players, plus girlfriends, spouses, hangers-on… two hundred bucks evaporated out of my wallet before I left the field. That was my Monday night, September 10th.
The next morning, headset on before the open, I checked in with Jeff at Rosenthal and Jimmy O’Brien from Cantor Fitz. Brooklyn guy, voice like gravel and traffic horns.
“So, what’d you do last night, Jombo? More of that Chicago beer-league hayseed softball?”
I told him about the strikeout, the shots, the damage to my wallet. He laughed so hard I can hear his coffee spill.
Half an hour later, an airplane went through Jimmy’s trading room.
That was it.
One minute, we are busting balls about Irish car bombs and softball. Next minute, he’s gone. He never called back. Never got to walk his dogs again. Never held his five-week-old son again. Jimmy’s name is carved in marble at Ground Zero now.
That is why this word is in the Grabber section today: Squander.
I never stepped into another batter’s box after that and I have never squandered a day since. That is why I write these chalkboards. That is why I point out the sun, the moon, the planets, the stars. That is why I use the word astonishing so much. Because every damn day is.
September 10th is a day to live for the people who didn’t get September 12th. Take the dogs for a walk. Call your parents if you still can. Meet a friend for oysters. Order the cannoli and the glass of port. Tell your kids you love them twice, not once.
Jimmy O’Brien’s children are adults now. He never had the chance to watch them grow up and that is why we never forget.
Because one day, without warning, we will all have our Monday night.
Don’t squander today.